


Run-In With Trouble (or Five Times Jess Meets Dean Winchester)

by bewarethesmirk



Category: Supernatural
Genre: F/M, Pre-Series
Language: English
Status: Completed
Published: 2016-04-01
Updated: 2016-04-01
Packaged: 2018-05-30 10:47:01
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,474
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6420751
Author URL: https://archiveofourown.org/users/bewarethesmirk/pseuds/bewarethesmirk
Summary: <blockquote class="userstuff">
              <p>Attractive, mysterious guys with devil-may-care attitudes are more trouble than they’re worth, and she doesn’t have time for that.</p>
            </blockquote>





	Run-In With Trouble (or Five Times Jess Meets Dean Winchester)

**Author's Note:**

> My first SPN fic, written for the 2016 round of SPN Spring Fling, for vilabelle's prompt "escaping jail."
> 
> Thanks to Dorian for the fabulous beta work!

The fifth time Jessica Moore meets Dean Winchester, it’s the final time.

*

By this time of night, Jess straddles the edge of human and zombie. She stares at the clock next to the cash register that indifferently remains 11:04 p.m. She’s tired of the smell of coffee and the endless emo soundtrack. A little less than an hour till her shift ends, and then there’s another hour of closing up before she can finally go to the library and study for her chemistry exam.

_Goodie. Like eating wheat bran for dessert._

She brushes up stray grounds in front of the espresso machine and half listens to Fiona Apple whine about heartbreak.

Two songs later, Jess is still darting glances at the clock when the door opens and she looks up—and keeps looking.

The guy walks in like he owns the place, set off sharply from the rest of the Stanford students slumped over tables imbibing coffee like it’s the nectar of life. The guy’s swagger kicks up a notch when he sees Jess, and she doesn’t look away when he makes too-direct eye contact.

He’s tall, gorgeous, broad shoulders—the works. Beat-up leather jacket that’s too big over a black t-shirt, ridiculously raggedy jeans and worker’s boots. Half of Jess’s mind is adding up all the bad boy clichés right down to the attractive stubble, but the rest of her gets stuck on his stupidly green eyes.

When he gets to the register, she turns up her smile so it’s a step above her customary customer service smile. “What can I get you?”

“Hmm.” He observes the chalkboard menu hanging behind her and holds a finger up to his mouth, like he’s proposing a genius idea. “Jack on the rocks?”

“Yeah, I wish.”

She’s wearing the usual Jolt barista uniform—black t-shirt and jeans—but the way he looks her up and down make her feel like it might as well be a bikini. Jess can’t quite figure out if she’s pleased or insulted.

Stupid eyes. Stupid freckles.

“I can make that happen.”

“What?”

“There are plenty of bars.” The guy nods towards the row of cheap bars across the street and eyes the clock. “What time does your shift end?”

_Come on, Jess. You know better than this_.

She can feel the easy answer sitting on her tongue. She could skimp on closing up and be out a little after midnight. Drink and flirt and maybe make out with a good-looking guy with “issues” written all over him.

Attractive, mysterious guys with devil-may-care attitudes are more trouble than they’re worth, and she doesn’t have time for that.

“In about an hour,” she says and shrugs. “Then I have the pleasure of going to the library and studying all night.” At least it’s not at lie.

“I’m sure I can change your mind.” He winks at her. It’s so brazen and ridiculous that she laughs.

“I’m afraid you can’t.”

“Ah, tough sell,” he says, his smile turns rueful. His eyes return to the chalkboard overhead. “I’ll have a redeye.”

Jess thinks of Sam, whose favorite drink in a tough spot is a redeye.

“Sure,” Jess says, muscle memory taking over as she reaches for a cup and holds the sharpie over it. “Name?”

“About time you asked,” he says, teasing with an edge of bite. “Dean.”

“Dean,” she repeats, writing it on the cup in her neat handwriting.

She takes his money, and while she pulls the shot she catches him staring a few times, and at least once frankly staring at her breasts, but he doesn’t say anything else. She tells herself to be glad as he walks out, beat-up jacket and beat-up jeans. She knew trouble when she saw it. But even trouble was worth a long look when it came wrapped up like that.

Through the glass, she sees him affectionately pat the roof of a sleek retro car that seems half-familiar. That black car sticks with her as she closes up, the nagging familiarity of it. But she never places where she’s seen it before.

*

A few days later, Jess is in a bar, three martinis deep, trying to make her disastrous dating life less of a disaster. Or possibly more or a disaster. Jury’s still out on that one.

She takes another sip from her martini and thinks of Sam and takes a larger sip. Jess sure knows how to pick them. Find her a cute, emotionally unavailable guy who sends constant mixed messages and has some weird hang-ups? Apparently, Jess is all over that.  

So here she is at a bar on a Saturday. Amy has already left with her latest conquest, and Jess is knocking back her martini like it’s water and pushing her luck that the bartender won’t think to check her ID. It’s the boobs, Amy always says, and Amy is usually dead right when it comes to the bitter upsides of sexism.

After sitting at the bar alone for half an hour and warding off half a dozen douches who are getting more and more interested the drunker she gets, Jess hits the low point of sad and pathetic and fumbles her wallet out of her purse to head home. Then a glass of something amber appears in front of her. She lifts her head with a curt, “Thanks, but no thanks” all queued up.

But then she halts, knows who it is before she even gets to his face because of that damn leather coat.

That’s, of course, the second time she meets Dean.

“Jack on the rocks.”

He drops down lightly on the barstool next to her and gives her a considering look.

“Dean,” she says, before she thinks it through.

He grins, boyish and pleased. “You remember.”

Her face warms but she brazens it out. “I have a good memory.”

“Me, too,” he says, waggling his eyebrows while he downs his shot. He wipes his mouth and Jess can’t keep from staring at it.

The flannel shirt worn open over his faded Zeppelin t-shirt is a juxtaposition that wasn’t entirely unappealing.

“So,” Dean says, sliding a bit closer.

“So?” she echoes, eyebrows raised.

She waits for something like a come-on, but what she gets instead is: “Have you heard about the frat boy who came to a very messy end this week?”

It’s so unexpected that Jess blinks hard and reaches for the glass of whiskey for something to do with her hands.

“What makes you think I know anything about that?” Jess asks, then chases the question with a burning gulp of whiskey.

“C’mon,” he says, “The coffee shop you work in is right off Greek row. Surely you heard or saw something.”

And it’s true. Jess had overheard snippets of conversation the first few days after it happened. The guy had been murdered brutally. Kids talked of the river of blood running under the door and down the hall.

Of all her friends, Sam seemed at turns the most interested and uninterested in the events, listening whenever it came up but never asking questions. A decent middle ground between curiosity and respect for the dead.

There must have been something telling on her face, because Dean’s expression has lost some of its playfulness. For the first time Jess notices that he looks like he hasn’t slept in several days.

“What’s your name?” he asks.

She finds herself telling him. And not only that, she finds herself letting him buy a couple more Jacks and finds herself divulging everything about Jason’s murder that she knows. How people say he was torn to pieces and all that blood dripping down the stairs. And the door was locked from the inside. Freaky stuff.

Dean is easy to talk to—almost like Sam, she finds herself thinking, then pushes the thought away. Dean is obviously a piece of work given how he flirts with the bartender and her almost indiscriminately, but there is something about him that makes her want to trust him against her better judgment. Or maybe she’s just drunk.

“Are you some kind of private investigator?” she asks, trying to put together the pieces.

He smirks. “You could say that.” He studies her for a moment. Jess allows it.

“So what’s a girl like you doing working in a coffee shop?”

Jess should be offended, but she’s not. “Don’t want to live off just my parents’ money,” she says, finishes her drink, with the clink of ice cubes hitting glass.

“Smart girl,” Dean says, with a trace of bitterness, which gets covered up by an easy smirk and sharp knock on the bar to call for another round.

*

The third time Jess has the dubious pleasure of meeting Dean, it’s on one of the weirdest nights of her life.

After midterms are over, when Jess should be tucked tightly into her dorm bed catching up on her beauty sleep, she decides it’s a brilliant idea to get shitfaced with Becky.

Becky had invited her to the party and Becky had handed her shot after shot of the foulest vodka imaginable and Becky had roped their group of friends into a rowdy game of Truth or Dare. And, to top it off, Becky had been the one who had dared Jess to go streaking down the block.

Jess isn’t one to back down from responsibility. Becky might have instigated it and midterms might have compounded it, but it was all Jess’s doing—the blue lights, the handcuffs, the world spinning around her, the door slamming, the cops chuckling as she’s thrown into the drunk tank.

One moment she had been buck-ass naked and giggling down the block and the next she is trapped with the world spinning uncontrollably around her.

Vomiting into a prison toilet was not on Jess’s Grand Life Plan.

Jess wakes later in her cell feeling stone cold sober. At some point, she had been given a drab gray jumpsuit to wear.

_Great, prison chic._

She looks around, her reality dawning on her. An arrest record. That was fabulous. Public indecency and underage drinking. She is never going to pass the bar.

She forces herself not to cry by biting her lip, putting her fingers to her temples and thinking. The detached rational part of her brain kicks in like it always did during emergencies.

_Gotta call Dad._

She’s moving to the front of the cell to get a cop’s attention, and she is greeted with about the last person she ever expected to see. For a second she wonders if she got roofied, if she’s hallucinating.

Dean. Dean in a well-fitting, if cheap suit. He flashes her a meaningful look as he is joined by a pudgy police officer.

“Good evening, ma’am.” Dean holds up a FBI badge. “Agent Cobain, FBI. I need to take you to headquarters to question you as a material witness.”

Her jaw drops, and she wants to ask questions. Was Dean an undercover agent? A material witness for _what_? How the fuck did he even know where to find her?

But another one of those looks from him, and she finds herself playing along.

“I guess,” she says.

The cop beside of Dean has a permanent scowl etched on his face but it becomes, if possible, more sour. “I still don’t like this. The girl at least needs some paperwork.”

“Ain’t got time for red tape,” Dean says and nods toward Jess. “Let her out.”

“Fine, but this reeks of malarkey."

“Better than your cologne,” Dean throws over his shoulder as they walk out, leaving the asshole of a cop to mutter behind them.

“What the hell, Dean?” she demands once she’s in his car and they’ve driven a safe distance away. She slaps him on the arm and—because it feels cathartic—she repeats the gesture until she feels much better.

 “You done yet?” he asks, glancing sidelong at her.

“Maybe,” she says.

He looks at her as passing headlights cast his hair golden.

“I have questions I want answered: how did you know where I was? Are you really an undercover agent? I somehow doubt it with that cheap suit.”

“Hey!” Dean says, running his fingers over the leg of his pants, as if soothing its feelings. “This suit is awesome.”

Jess smiles despite herself.

“Really,” she says, smacks his arm again. “Tell me.”

Dean sighs. “Bossy.” He swerves over into a parking lot, cuts the ignition and turns to her. “I ain’t telling you much, sweetheart.”

“We’ll see.”

She learns more than she expected. Not so surprisingly, he’s not an undercover agent, but he won’t tell her what he is or what he does. He sums it up that she should be grateful and not look a gift horse in the mouth.

He drives her home, idling in front of her dorm, and he cuts the ignition again.

“So, I’ve helped you escape from jail. Does that get me an invite upstairs?”

She slaps him on the arm again and doesn’t even bother to say no.

“Kinky,” he says and shrugs.

She rolls her eyes, but who can blame her if she leaves him with a kiss on the cheek.

*

The fourth time Jess meets Dean, it’s right after Sam turns her down the first time. It’s the next night and she meets him in the same bar. He’s already settled in with a beer when she arrives.

“Fancy meeting you here,” she says.

Dean looks up, surveys her with a shrewd expression and orders a drink for her.

“What’s gone wrong now?” he asks her and to her surprise, he sounds fairly genuine for a strange, creepy, hot guy who keeps making half-hearted attempts to get into her pants.

She tells him. About Sam, the boy who she loves but isn’t ready for anything “complicated.” She doesn’t understand why it has to be complicated.

Dean doesn’t try to stop the whole sad purging and she keeps talking and drinking till she’s said too much.

Again, Dean drives her home. “He’ll come around,” Dean says. “He’d be a fool not to.”

Jess tries to smile and chastises herself for being so maudlin. “You’re right,” she says before she leans over and kisses Dean full on the mouth, chaste and soft. To her surprise, he pulls away after just a moment.

Jess clears her throat awkwardly. “Well, good night.” She opens the car door, ignoring her tingling mouth. “Thanks for the ride.”

“Any time,” he says, with a funny salute and one last smile, and he drives off.

Later she realizes she never asked for his number.

*

The fifth time is when Jess finally learns that Dean is Dean _Winchester_ , the mysterious but heavy absence in Sam’s life.

When Sam comes back for his interview, Jess intends to tell Sam about Dean.

She never gets the chance.


End file.
